DE2241731C3 - Triensteroid-Verbindungen, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen - Google Patents

Triensteroid-Verbindungen, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen

Info

Publication number: DE2241731C3
Authority: DE; Germany
Prior art keywords: ketal; general formula; gona; group; oxo
Prior art date: 1971-08-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

DE2241731A

Other languages

German (de)

English (en)

Other versions

DE2241731A1 (de

DE2241731B2 (de

Inventor

Genevieve Dr. Paris Azadian

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1971-08-26

Filing date

1972-08-25

Publication date

1982-05-06

1972-08-25 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1973-03-08 Publication of DE2241731A1 publication Critical patent/DE2241731A1/de

1981-06-19 Publication of DE2241731B2 publication Critical patent/DE2241731B2/de

1982-05-06 Application granted granted Critical

1982-05-06 Publication of DE2241731C3 publication Critical patent/DE2241731C3/de

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title claims 2
-1 Triene steroid compounds Chemical class 0.000 title description 8
239000000543 intermediate Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
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125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
229960001124 trientine Drugs 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000003500 enol ether group Chemical group 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
125000002524 organometallic group Chemical group 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000003431 steroids Chemical class 0.000 claims description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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239000000203 mixture Substances 0.000 description 19
239000000047 product Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000002329 infrared spectrum Methods 0.000 description 10
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
229960001712 testosterone propionate Drugs 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002280 anti-androgenic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
210000002307 prostate Anatomy 0.000 description 3
210000001625 seminal vesicle Anatomy 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
201000010653 vesiculitis Diseases 0.000 description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
150000004057 1,4-benzoquinones Chemical class 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
238000006027 Birch reduction reaction Methods 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
239000012043 crude product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
238000005907 ketalization reaction Methods 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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238000010992 reflux Methods 0.000 description 2
230000028327 secretion Effects 0.000 description 2
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
IKZOMJGRWIOEDP-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxolane Chemical compound ClCC1OCCO1 IKZOMJGRWIOEDP-UHFFFAOYSA-N 0.000 description 1
GAOQAPRPYXWTFK-UHFFFAOYSA-N 2-methyl-2-phenyl-1,3-dioxolane Chemical compound C=1C=CC=CC=1C1(C)OCCO1 GAOQAPRPYXWTFK-UHFFFAOYSA-N 0.000 description 1
CJWVIHVWKIOTNB-UHFFFAOYSA-N 2-methyl-2-prop-1-en-2-yl-1,3-dioxolane Chemical compound CC(=C)C1(C)OCCO1 CJWVIHVWKIOTNB-UHFFFAOYSA-N 0.000 description 1
XESXYNJRSXSQNG-UHFFFAOYSA-N 2-methyl-4-[(4-methylphenyl)methyl]-1,3-dioxolane Chemical compound CC1OCC(O1)CC1=CC=C(C=C1)C XESXYNJRSXSQNG-UHFFFAOYSA-N 0.000 description 1
HDEXQZFQDZGFLQ-UHFFFAOYSA-N 4,5-dibromo-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound BrC1=C(Br)C(=O)C(C#N)=C(C#N)C1=O HDEXQZFQDZGFLQ-UHFFFAOYSA-N 0.000 description 1
AQZMINLSVARCSL-UHFFFAOYSA-N 4-chloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound ClC1=CC(=O)C(C#N)=C(C#N)C1=O AQZMINLSVARCSL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
241001086018 Homo heidelbergensis Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
206010046788 Uterine haemorrhage Diseases 0.000 description 1
206010046793 Uterine inflammation Diseases 0.000 description 1
CIHXIRAAMAUYLZ-UHFFFAOYSA-N [K+].[K+].[C-]#[C-] Chemical compound [K+].[K+].[C-]#[C-] CIHXIRAAMAUYLZ-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
230000003388 anti-hormonal effect Effects 0.000 description 1
230000002158 anti-implantation Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000027455 binding Effects 0.000 description 1
238000009739 binding Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
LIJDDOXRYWAXQG-UHFFFAOYSA-N tripentoxyalumane Chemical compound CCCCCO[Al](OCCCCC)OCCCCC LIJDDOXRYWAXQG-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE2241731A 1971-08-26 1972-08-25 Triensteroid-Verbindungen, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen Expired DE2241731C3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7131032A FR2150254B1 (ru)	1971-08-26	1971-08-26

Publications (3)

Publication Number	Publication Date
DE2241731A1 DE2241731A1 (de)	1973-03-08
DE2241731B2 DE2241731B2 (de)	1981-06-19
DE2241731C3 true DE2241731C3 (de)	1982-05-06

Family

ID=9082246

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2241731A Expired DE2241731C3 (de)	1971-08-26	1972-08-25	Triensteroid-Verbindungen, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen

Country Status (17)

Country	Link
US (1)	US3790564A (ru)
JP (1)	JPS5617359B2 (ru)
AU (1)	AU471590B2 (ru)
BE (1)	BE787898A (ru)
CA (2)	CA974228A (ru)
CH (1)	CH554855A (ru)
DD (1)	DD99366A5 (ru)
DE (1)	DE2241731C3 (ru)
DK (1)	DK131189B (ru)
FR (1)	FR2150254B1 (ru)
GB (2)	GB1386439A (ru)
HU (1)	HU163773B (ru)
IL (1)	IL40022A (ru)
NL (1)	NL176366C (ru)
SE (1)	SE385709B (ru)
SU (1)	SU446965A3 (ru)
ZA (1)	ZA725814B (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4055562A (en) *	1975-10-06	1977-10-25	Sterling Drug Inc.	Process for preparing pregn-20-yne compounds and novel product produced thereby
FR2522328B1 (fr) *	1982-03-01	1986-02-14	Roussel Uclaf	Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments

0
- BE BE787898D patent/BE787898A/xx not_active IP Right Cessation
1971
- 1971-08-26 FR FR7131032A patent/FR2150254B1/fr not_active Expired
1972
- 1972-07-28 CH CH1128672A patent/CH554855A/fr not_active IP Right Cessation
- 1972-07-28 IL IL40022A patent/IL40022A/xx unknown
- 1972-08-15 US US00280852A patent/US3790564A/en not_active Expired - Lifetime
- 1972-08-21 GB GB3886172A patent/GB1386439A/en not_active Expired
- 1972-08-21 GB GB3160074A patent/GB1386440A/en not_active Expired
- 1972-08-23 ZA ZA725814A patent/ZA725814B/xx unknown
- 1972-08-23 SU SU1821082A patent/SU446965A3/ru active
- 1972-08-24 HU HURO674A patent/HU163773B/hu unknown
- 1972-08-24 DD DD165226A patent/DD99366A5/xx unknown
- 1972-08-25 JP JP8471072A patent/JPS5617359B2/ja not_active Expired
- 1972-08-25 DE DE2241731A patent/DE2241731C3/de not_active Expired
- 1972-08-25 NL NLAANVRAGE7211612,A patent/NL176366C/xx not_active IP Right Cessation
- 1972-08-25 AU AU45973/72A patent/AU471590B2/en not_active Expired
- 1972-08-25 SE SE7211051A patent/SE385709B/xx unknown
- 1972-08-25 CA CA150,245A patent/CA974228A/en not_active Expired
- 1972-08-28 DK DK424472AA patent/DK131189B/da unknown
1974
- 1974-10-02 CA CA210,609A patent/CA996546A/fr not_active Expired

Also Published As

Publication number	Publication date
CA996546A (fr)	1976-09-07
JPS4832859A (ru)	1973-05-02
SU446965A3 (ru)	1974-10-15
AU471590B2 (en)	1976-04-29
DK131189B (da)	1975-06-09
JPS5617359B2 (ru)	1981-04-22
CA974228A (en)	1975-09-09
DE2241731A1 (de)	1973-03-08
GB1386439A (en)	1975-03-05
NL176366C (nl)	1985-04-01
IL40022A0 (en)	1972-09-28
US3790564A (en)	1974-02-05
FR2150254A1 (ru)	1973-04-06
NL7211612A (ru)	1973-02-28
DD99366A5 (ru)	1973-08-05
HU163773B (ru)	1973-10-27
FR2150254B1 (ru)	1974-10-18
ZA725814B (en)	1973-10-31
BE787898A (fr)	1973-02-23
CH554855A (fr)	1974-10-15
IL40022A (en)	1975-10-15
NL176366B (nl)	1984-11-01
GB1386440A (en)	1975-03-05
DE2241731B2 (de)	1981-06-19
DK131189C (ru)	1975-11-17
AU4597372A (en)	1974-02-28
SE385709B (sv)	1976-07-19

Publication	Publication Date	Title
CH561739A5 (en)	1975-05-15	4-Hydroxy-2-butenoic acid lactone steroid derivs - cardiotonic, anti-inflammatory, hypocholesterolaemic, mineralocorticoid agents
DE1468950C3 (de)	1978-11-30	Verfahren zur Herstellung von 3-0x0-4,9-11-triensteroiden und einige dieser Verbindungen
DE1543852A1 (de)	1970-03-05	Verfahren zur Herstellung von Furanverbindungen
DE2241731C3 (de)	1982-05-06	Triensteroid-Verbindungen, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen
DE2226552C3 (de)	1982-05-19	Ungesättigte 17 β -Cyano-Steroidderivate, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen
DE2037403C3 (de)	1980-04-30	3-OXO-7 a , 17 a -dimethyl- 13 ß -äthyl-17 ß -hydroxy-gona-4,9,11-trien, Verfahren zu seiner Herstellung, dabei auftretende Zwischenprodukte sowie Arzneimittel
DE1643005C3 (de)	1975-05-22	15,16beta-Methylen-testosterone, Verfahren zu ihrer Herstellung sowie diese Steroide enthaltende Mittel
DE1468985A1 (de)	1969-08-07	17alpha-Alkyl-,17alpha-Alkenyl- und 17alpha-Alkinyl-4,5-epoxy-19-norandrostan-17beta-diole und deren Carbonsaeureester sowie Verfahren zur Herstellung dieser Verbindungen
DE1188079B (de)	1965-03-04	Verfahren zur Herstellung von 17alpha, 21-Dioxysteroiden
DE2109853C3 (ru)	1980-02-21
DE1768700B1 (de)	1972-04-27	Ungesaettigte 2,2-Dimethyl-steroide der OEstran- bzw.Gonanreihe und Verfahren zu ihrer Herstellung
DE1593052B2 (de)	1974-08-15	Verfahren zur Herstellung von 16-Methylen-19-norprogesteron-derivaten
DE1793608B1 (de)	1972-05-04	17alpha-Alkyl-,-Alkenyl- oder -Alkinyl-13ss-alkylgon-4-oder-5(10)-en-17ss-ol-3-one
DE1593311C (de)	1972-01-27	Verfahren zur Herstellung des 10,11 Lactons der 3 Oxo 11 beta, 17 beta dihydoxy 17 alpha athinyl ostra 4 en 10 beta carbon saure
DE2158260C3 (de)	1976-07-01	11-Alkoxysteroide, Verfahren zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen
DE1468632C (de)	1971-04-15	öalpha Acetylthio 4 en 3 on steroide und Verfahren zu deren Herstellung
DE1793608C (de)	1972-12-14	17alpha-Alkyl-, -Alkenyl- oder -Alkinyl-13beta-alkylgon-4- oder -5(10)-en-17betaol-3-one. Ausscheidung aus: 1468604
DE1793749C3 (de)	1976-03-04	Verfahren zur Herstellung von 1,4-Diensteroiden
DE1468421C (de)	1973-05-17	Neu 9beta,10alpha Steroide der Pregnanreihe und Verfahren zu ihrer Herstellung
DE1443636A1 (de)	1969-11-20	Verfahren zur Herstellung neuer Methylandrostene
DE2160522A1 (de)	1972-06-29	Verfahren zur Herstellung von 14 beta, 18- und 5 beta, 19-(Epoxyäthanoimino)steroiden
DE1643035B2 (de)	1976-01-15	15beta,16beta-methylen-5alpha -androst-l-ene, verfahren zu deren herstellung sowie diese enthaltende mittel
DE1174778B (de)	1964-07-30	Verfahren zur Herstellung von 3, 4-Dimethyl-?-oestratrien-1, 17ª‰-diol
DE1643054A1 (de)	1971-04-15	Neue 7-Methylsteroide
DE1249268B (de)	1967-09-07	Verfahren zur Herstellung von 1 7a-Dimethyl - A1 - androstcnolondenvaten

Legal Events

Date	Code	Title
1979-07-26	OD	Request for examination
1982-05-06	C3	Grant after two publication steps (3rd publication)
1984-08-09	8339	Ceased/non-payment of the annual fee